Homoharringtonine (1), a rather complex ester of cephalotaxine (from cephalotaxus harringtonia), has been found to possess anti-leukemic activity. Its further clinical testing is hindered by its scarcity from plant sources. No total or partial synthesis of (1) has been reported up to date, although attempts were made to obtain (1) by the esterification of cephalotaxine, co-occurring in abundant quantities with (1) in the cephalotaxus species, with the proper side-chains. It is the aim of this project to investigate: a) the oxidative conversion of synthetic cephalotaxine to drupacine, which possesses more favorable steric arrangement of the hydroxyl group. b) esterification of drupacine with proper side chains and removal of the ether-acetal bridge to produce harringtonine alkaloids. c) a novel synthesis of cephalotaxine starting with commercially available enamine (10), should the criteria in a, and b, be met, in order to ease the demand on natural sources. The availability of small samples of cephalotaxine, hydroxycephalotaxine and drupacine will permit conclusions to be reached rather quickly. Furthermore, the proposed synthesis of cephalotaxine itself involves a novel variant of the vinylcyclopropyl rearrangement which merits investigation, in view of its potential applicability to the synthesis of heterocyclic systems.